13494-07-0
| Molecular & Flavor Profile | |
|---|---|
| Common name: | 13494-07-0 |
| IUPAC name: | 3,5-dimethylcyclopentane-1,2-dione |
| SMILES: | CC1CC(C(=O)C1=O)C |
| CAS: | 13494-07-0 |
| Flavor Profile: | caramel, sweet, maple |
| FEMA Flavor Profile: | Savory |
| FEMA Number: | 3269 |
| Taste: | pleasant, bitter taste |
| Odor: | odor of burnt sugar |
| Functional Groups: | carbonyl compound, ketone |
Physicochemical Properties
- Molecular weight: 126.155 g/mol
- HBD count: 0
- HBA count: 2
- Number of rotatable bonds: 0
- Complexity: 142.0
- Topological Polor Surface Area: 34.1 A^2
- Monoisotopic Mass: 126.068 g/mol
- Exact Mass: 126.068 g/mol
- XlogP: 0.7
- Charge: 0 C(coulomb)
- Heavy Atom Count: 9
- Atom Stereocenter Count: 2
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 2
- Bond Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently Bonded Unit Count: 1
- InChI: InChI=1S/C7H10O2/c1-4-3-5(2)7(9)6(4)8/h4-5H,3H2,1-2H3
- Volume 3D: 104.1
Nomenclature
- Common name: 13494-07-0
- IUPAC name: 3,5-dimethylcyclopentane-1,2-dione
- CAS numbers: 13494-07-0
- SMILES: CC1CC(C(=O)C1=O)C
- InChI: InChI=1S/C7H10O2/c1-4-3-5(2)7(9)6(4)8/h4-5H,3H2,1-2H3
- FlavorDB/FEMA name: 3,5-DIMETHYL-1,2-CYCLOPENTADIONE
- Synonyms: 1,2-Cyclopentanedione, 3,5-dimethyl-; 3,5-Dimethylcyclopentane-1,2-dione; 3,5-Dimethyl-1,2-cyclopentadione; 3,5-Dimethyl-1,2-cyclopentanedione
- FL number: 7.076
- NAS number: 3269
- CoE number: 2235
- EINECS number: 236-811-3
- JECFA number: 421
Regulatory Status
- CoE status: 5 ppm
- JECFA status: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1998)
Aroma/Taste Threshold Values
- Aroma threshold values: 1 ppm
- Taste threshold values: Taste characteristics at 10 ppm; brown, sweet, sugary, maple, caramellic
Composition
- Molecular formula: C7H10O2
- Molecular composition: C: 0.666, H: 0.080, O: 0.254
- Number of atoms: 9
ADMET Properties
- ADMET Solubility: -1.9069999999999998
- ADMET Solubility Level: 4.0
- ADMET BBB: -0.33
- ADMET BBB Level: 2.0
- ADMET EXT Hepatotoxic: -2.3741
- ADMET EXT Hepatotoxic prediction md: True
- ADMET EXT Hepatotoxic applicability: All properties and OPS components are within expected ranges.
- ADMET EXT Hepatotoxic applicability md: 6.04796
- ADMET EXT Hepatotoxic applicability mdpvalue: 0.999976
- ADMET Absorption Level: 0.0
- ADMET EXT PPB: -2.12628
- ADMET EXT PPB prediction: True
- ADMET EXT PPB applicability: All properties and OPS components are within expected ranges.
- ADMET EXT PPB applicability md: 7.351189999999999
- ADMET EXT PPB applicability mdpvalue: 1.0
- ADMET unknown AlogP98: 0.0
- ADMET AlogP98: 1.203
- ADMET PSA 2D: 34.601
2D/3D Properties
- Number of atoms: 9
- Molecular formula: C7H10O2
- Molecular composition: C: 0.666, H: 0.080, O: 0.254
- Molecular mass: 126.068 g/mol
- Energy: 21.25 Kcal/M
- AlogP: 1.203
- LogD: 1.203
- Molecular Solubilty: -1.135
- Number of aromatic bonds: 0
- Number of aromatic rings: 0
- Number of H acceptor: 2
- Number of H acceptor lipinski: 2
- Number of H donor: 0
- Number of H donor lipinski: 0
- Number of H bonds: 0
- Number of rings: 1
- Surface area(SA): 140.28 A^2
- Molecular SASA(Solvent accessible SA): 279.619 A^2
- Radius of gyration: 1.37046 A
- Molecular 3D SASA: 271.481 A^2
Consumption
- Consumption: 533.33 lb
- Individual intake: 0.0004519 mg/kg/day
- Trade association guidelines: 1.004 mg
- IOFI: Nature Identical
Specifications
- Specifications: (JECFA, 2000); Appearance; Light yellow to yellowish brown ; powder; Specific gravity; 0.5 g/mL (20°C); Assay (min); 98%; Solubility; Insoluble in water; Melting point; 87–93°C
Reported Uses
- Reported uses (ppm): (FEMA, 1994)
-
Food category usual/max:
Food category Usual (ppm) Max (ppm) Baked goods 3.30 3.30 Reconstituted vegetables 4.00 4.00 Breakfast cereals 2.80 3.30 Seasonings, flavorings 5.00 5.00 Frozen dairy 6.00 6.00 Soft candy 4.10 7.80 Nonalcoholic beverages 3.00 5.20 Sweet sauce 0.78 21.00
Synthesis
- Synthesis: By direct alkylation of the methyl ester of the commercially available 3-methylcyclo-pent-2-en-2-ol-1-one, followed by the cleavage of the ether function
Physical-Chemical Characteristics
- Empirical formula / MW: C7H10O2/126.15CH3OOCH3
Details of "Molecular & Flavor Profile" and physicochemical properties were obtained from PubChem Substance & Compound Databases, FooDB, Flavornet, SuperSweet, and BitterDB. 2D/3D and ADMET properties were obtained with Discovery Studio.